Do the responsibilities that come with age inevitably erode the ideals of youth? Can women achieve the most in their careers while enjoying a fully satisfying family life? Is sadness a natural — as opposed to pathological — response to the realization that life will not bring us everything we had hoped it would?

These questions resonate today as strongly, and at times as painfully, as they did when Wendy Wasserstein’s most celebrated play, “The Heidi Chronicles,” stormed Broadway in 1989, going on to win the best play Tony Award and the Pulitzer Prize the next year. They are being posed once again, with the same bright humor and reflective intelligence, in the vibrant revival that opened at the Music Box Theater on Thursday night, led by a softly radiant Elisabeth Moss in the title role.

Ms. Moss, a superb actor who possesses an unusual ability to project innocence and smarts at the same time, inherits a role played by many since Joan Allen originated it when the play had its premiere at Playwrights Horizons Off Broadway. (I saw Mary McDonnell, one of several who succeeded Ms. Allen during the play’s long Broadway run; Jamie Lee Curtis played the role in a television movie.) Known for her demure but ambitious Peggy in “Mad Men,” Ms. Moss puts her own distinctive stamp on the part. As Heidi Holland grows from a burgeoning feminist in the 1960s to a high-achieving but emotionally fragile art historian in the 1970s and ’80s, Ms. Moss is constantly questioning both her own choices and those of the circle of friends and lovers who surround her.

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From left, Tracee Chimo, Elise Kibler and Elisabeth Moss, who portrays the title character, Heidi Holland, in this play directed by Pam MacKinnon.CreditSara Krulwich/The New York Times

Ms. Moss’s affecting Heidi may lack the confidence that others possess or project. But loyalty to her intelligence and her authenticity of feeling — including the right to feel both “worthless” and “superior” at the same time — are the lodestars that keep her from succumbing to debilitating doubt as she watches relationships wither or evolve.

I’ll admit to some anxiety on the question of the play’s durability. Much of its humor is grounded in gentle satire of the specific experiences and obsessions of the baby boom generation — matters that might seem to have sprung from a time capsule today. (Um, Bert Lance — who he?) Would gags about radical feminism still land in the age of Sheryl Sandberg’s “Lean In”?

Fortunately, under the direction of Pam MacKinnon and in the hands of a fine supporting cast, notably Jason Biggs and Bryce Pinkham as the men in (and largely out) of Heidi’s life, the play’s humor retains its buoyancy, even when the specific matters at hand — the politics of the Vietnam era, or the consciousness-raising mania that fed the women’s rights movement in the 1970s — have acquired the distancing patina of textbook history. Projections by Peter Nigrini, John Lee Beatty’s detailed sets and a nifty retro-pop soundtrack help to vividly evoke the passing decades. And the immense popularity of “Lean In” and books about the motherhood-vs.-career debate attest to how germane the play’s questions remain, notwithstanding the strides women have made since its premiere.

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Elisabeth Moss and Bryce Pinkham in "The Heidi Chronicles."CreditSara Krulwich/The New York Times

We first meet Heidi in high school, evincing the insecurity about engaging with the opposite sex that will remain a nagging problem, one that her best friend, Susan (a tartly funny Ali Ahn), doesn’t possess, as she hitches up her skirt and goes on the prowl. Fortunately, the fragrance of the wallflower has an allure for Peter Patrone (Mr. Pinkham), who rescues Heidi from her abandonment by making witty repartee that signals — perhaps a little too archly, in Mr. Pinkham’s boisterous reading — that he will not be the romantic answer to Heidi’s dreams. (Happily, Mr. Pinkham’s performance grows much more nuanced, and ultimately very moving, as Peter matures into a doctor running a children’sward.)

Both Susan and Peter remain touchstones in Heidi’s life, as does Scoop Rosenbaum (Mr. Biggs), the man she meets a few years later, at a dance for Eugene McCarthy in New Hampshire, where Heidi feels almost as awkward as she did in high school. He pours on the glib charm — Mr. Biggs comes by it naturally — and casually suggests they sleep together. Despite his strong attraction to her intelligence and independence, Scoop has an eye on the main chance, meaning his own, and eventually marries a less smart but more accommodating woman, Lisa (Leighton Bryan).

As she moves through life, Heidi instinctively resists simple dichotomies, whether they are promulgated by the radical feminist Fran (played with sensationally funny zest by Tracee Chimo), whose mantra is “Either you shave your legs or you don’t,” or by Scoop, who believes that a man and woman who marry and both seek self-fulfillment will be “competing with each other.” But Heidi’s faithfulness to her fundamental beliefs — among them that “all people deserve to fulfill their potential” — ultimately leaves her feeling adrift as the moat of middle age approaches.

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Elisabeth Moss and Bryce Pinkham in a scene from the Broadway revival of Wendy Wasserstein’s play, at the Music Box Theater.Published OnMarch 19, 2015

Wasserstein, who died at 55 in 2006, structured the play as an animated tableau of the turning points in Heidi’s life, an episodic style that can be tricky, leading to surface-skimming or blunt point-making. But the writing is, for the most part, so sharp and precisely observed, despite its wide scope, that we rarely feel any shortcuts are being taken.

On occasion the jokes can be a little stretched, even when, as in the (implausible) talk show scene, they are hilariously handled by the cast. Nor does Wasserstein always avoid cliché, as when Scoop tells Heidi, in soap-opera-ese, “I never meant to hurt you.” But throughout the play her keen ear for comic absurdity grounded in truth is matched by a probing compassion for her characters, even when they are viewed through a sardonic lens.

For me, the moving heart of “The Heidi Chronicles” remains the wonderful monologue in the second act. Heidi is speaking at a gathering of her high school alumnae, but instead of the usual manicured, upbeat speech, she delivers an off-the-cuff, emotionally exposed anecdote. It’s really a play in itself, about the sense of alienation she felt that day from other women in a gym locker room: women she respects and admires, in some senses, but whose choices to pursue life’s more superficial rewards leave her feeling “stranded.”

Ms. Moss, her eyes moistening even as her voice remains strong, delivers this beautiful speech with a grace that grows stronger as Heidi’s peppery, self-aware humor gives way to lacerating honesty. Those are, as it happens, key notes in Wasserstein’s durable play, and Ms. Moss and her collaborators in this sterling production sing them forth with a revitalizing warmth.